N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-((2S,3R,4S,5S,6R)-5-(benzoyloxy)-6-((benzoyloxy)methyl)-3,4-bis(benzyloxy)tetrahydro-2H-pyran-2-yl)-L-serine | 848827-42-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-((2S,3R,4S,5S,6R)-5-(benzoyloxy)-6-((benzoyloxy)methyl)-3,4-bis(benzyloxy)tetrahydro-2H-pyran-2-yl)-L-serine
• CAS: 848827-42-9
• 化学式: C₅₂H₄₇NO₁₂
• 分子量: 877.945
• InChiKey: JXIBPBIGGSMOCP-SYECEERFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  65.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  165.15
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-((2S,3R,4S,5S,6R)-5-(benzoyloxy)-6-((benzoyloxy)methyl)-3,4-bis(benzyloxy)tetrahydro-2H-pyran-2-yl)-L-serine 在 sodium methylate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 乙胺 、 1-羟基苯并三唑一水物 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Hexacosanoic acid [(S)-2-((2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1-tetradecylcarbamoyl-ethyl]-amide
  参考文献：
  名称：

  Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

  摘要：

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.027
• 作为产物：
  描述：

  [(2R,3S,4S,5R,6S)-3-benzoyloxy-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-prop-2-enoxypropoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-((2S,3R,4S,5S,6R)-5-(benzoyloxy)-6-((benzoyloxy)methyl)-3,4-bis(benzyloxy)tetrahydro-2H-pyran-2-yl)-L-serine
  参考文献：
  名称：

  Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

  摘要：

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.027